I guess I'm interested to see just how bad other people think it is and how much money I should throw at it. I'd love to hear any comments and ideas ...either high or low budget.

I think it looks pretty good now.... round and arched seems to be a theme. It does need some lush flower beds (eg.- native grasses, green leafy plants, purple, pink, and white flowers ,low maintenance type). I would try that first since it would be more inexpensive. Then just let it grow for a while....it may just distract from the windows you don't like.

getting a window and siding quote shouldn't be that hard. the indoor part patching the drywall can be done by a skilled handyman.

you can probably remove the grills yourself and that would change things right away.

I would also add cedar or cedar-looking shingles to the peaks to warm up the front.

The problem in estimating what this will cost - it is incredibly regional. At this time, some parts of the country are booming and you just cannot get skilled help for smaller jobs.